


Begging Pretty - Teamwork Seduction

by LeviSqueaks



Series: KiaSqueaks presents: Rare Pair Bingo [1]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blowjobs, Bottom Dean Winchester, Bottom Jimmy Novak (Supernatural), Cockwarming, Dean/Cas/Jimmy Square, Dirty Talk, Dom Castiel (Supernatural), Dom Castiel/Sub Dean Winchester, Dom Jimmy Novak (Supernatural), Dom!Cas, Dominant Bottom, Double Anal Penetration, Light BDSM, Light Dom/sub, M/M, Making Out in the Impala (Supernatural), Multi, SPN RarePair Bingo, Spanking, Sub Dean, Sub!Dean, Teamwork Seduction, Threesome, Top Castiel (Supernatural), dean and cas bingo - polyamory square, switch!jimmy
Language: English
Status: Completed
Published: 2020-02-27
Updated: 2020-02-27
Packaged: 2021-02-28 03:27:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,367
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22916953
Author URL: https://archiveofourown.org/users/LeviSqueaks/pseuds/LeviSqueaks
Summary: Castiel was sure of one thing, Jimmy always got what he wanted. When the twins come across a handsome stranger in a bar, they work together to bring him home and no one is disappointed at their success.
Relationships: Castiel/Jimmy Novak (Supernatural), Castiel/Jimmy Novak/Dean Winchester
Series: KiaSqueaks presents: Rare Pair Bingo [1]
Series URL: https://archiveofourown.org/series/1647163
Comments: 17
Kudos: 156
Collections: Dean and Cas Bingo, SPN Rare Ship Bingo 2020





	Begging Pretty - Teamwork Seduction

**Author's Note:**

  * For [MistressPandora](https://archiveofourown.org/users/MistressPandora/gifts).



> This is a Valentine for my wonderful Partner-In-Crime and ultimate bestie - Mistress Pandora. A girl couldn't ask for a better heterolifemate or sister. This story also fulfills the Dean/Cas/Jimmy square on my rarepair bingo card. 
> 
> ALSO: Jimmy's real name is Janiel. It's the angel of Tuesday. I'm proposing the twins were born on a Wednesday and their mom was still feeling the good drugs when she named them.

Dean was having a fantastic night. 

The beer was cold, the people were hot, and the music was just the right side of too loud. He had been playing pool with Sammy and Benny until both had begged off for the night. Sammy disappearing back to his books, and Benny beating it with some cute redhead that had led him off. He leaned against the bar, shifting to turn and look around the crowded space, eyes scanning until they landed on a man across the hazy room. 

He was tall, but not quite as tall as Dean, with messy black hair, tight jeans and a dark t-shirt that had a v-neck that seemed two inches too deep to be company appropriate. His skin was pale, and arms raised like he was in church as he danced, head thrown back while dancing to the pulsing beat. Dean’s eyes met the other man’s from across the room, his gut clenching at the piercing blue eyes that met his. Further swooping at the wide, bright grin that crossed over his face as the man gestured to Dean to come join him. 

Dean looked down, toying with his beer as a slight smile crossed his face but he turned away back to the bar. The man looked like sex on legs, but he hadn’t come out looking for a roll in the sack. Still, the thought of Blue Eyes sprawled out over Baby’s hood, head thrown back and moaning had him biting his lip as he sipped his beer. 

“Did you see someone interesting in the crowd?” A deep, gravelly voice sounded from Dean’s right, startling him as he turned to find the owner of the voice. Dean's breath sucked between parted lips at the sight of the man next to him. Pale skin, stubble sprawled across a strong jaw, mussed black hair that looked like someone had run their hands through it. He was wearing a burgundy shirt with a deep v that made his subtle muscle tone and delicate clavicles pop. Tight, tight dark blue jeans that hugged him like a second skin. It was the mystery dancer, with the bright blue eyes. 

“Yeah uh…” Dean’s voice dried up as he tried to clear it without being obvious at how affected he was by being near the man. How had he come up beside him without Dean noticing? The heat that radiated off of the other man as he shifted closer to Dean made him swoon. And blue eyes lit in interest though his expression was more stoic than it had been on the dance floor. “I think... you uh… know it was you.” 

“Aww, really?” A smoother, teasing voice said behind Dean from where he was facing the gorgeous man in front of him. “I had hoped it was me.”

Dean turned and stiffened, his mind blanking with shock as he found… the man from the dance floor. He was identically matched to the man behind him, except he was clean shaven and his visible skin shimmering with body glitter. 

“I saw you blush from across the room, I had hoped you would join me,” the second man added as he reached forward to trace a finger up Dean’s forearm. “What’s your name, Handsome?”

Dean blinked and stammered wordlessly, out of his element and flushing as his hand clenched around his beer. The heat radiating off the first man as he pressed closer, bumping up against his hip had Dean swallowing reflexively. It only grew worse as a sex laden voice responded behind him. “I’m Cas,” he rasped in Dean’s ear, tone low and promising as a whimper left Dean’s throat. 

The cleaner, brighter version in front of him leaned a little closer to Dean. He rested against the bar but with his body angled to mirror his doppelganger behind him, caging Dean in. He lifted his hand to trace up Dean’s stomach to his chest with an impish smile, blue eyes crinkling at the corners. “Jimmy,” he added. “You gonna let us whisk you away for a very good time, Handsome?” 

Dean swallowed, lifting his beer as a stalling tactic, his eyes taking in Jimmy as he cautiously leaned back into Cas. He shivered at the heat of the other man pressing solidly against him from knee to shoulder and cleared his throat again, a little raspy whimper leaving him. Fuck it. He was tipsy, he was horny and he… they were gorgeous and willing. “Dean, and don’t you dare threaten me with a good time unless you’re good for it.” 

Castiel chuckled as Jimmy gave him a wide smile and stole his beer to finish it. “Good boy,” he praised softly in Dean’s ear, earning a sucked in breath and a hand quickly anchoring on his hip. 

“Oooh Cas… I think he likes that,” Jimmy breathed as he leaned forward and pressed a kiss to Dean’s cheek then nuzzled closer to murmur in his ear over the sound of the music, “You’re gonna be very good for us Dean, and we’re going to take care of you.” 

Dean gave a wordless nod in response before he found himself being pulled away from the bar by identical hands, mind spinning in excitement. What the hell had he gotten himself in to? He had a feeling he was gonna love finding out.

~~~ 

The twins kept Dean occupied the entire drive. Dean found out they had ubered in, so they all piled into Baby, Cas behind him, leaning forward so his breath spilled over Dean's neck as he hummed along with the song on the radio, and Jimmy pressed beside him, a hand on his thigh and lips trailing across his neck and shoulder. 

Whenever Dean started to lose himself to the sensation he gripped the wheel tighter, his back ramrod straight even as soft whimpers left his throat at each little nip from Jimmy’s teeth. Jimmy pulled away from a playful bite as Dean groaned while they approached a light and he grinned back at Cas in the backseat. “I think he likes a little teeth.” He may have said more but the second the stopped at the light, Dean reached out and dragged Jimmy close to kiss him desperately, hands fisted in the t-shirt and snaking around his back in a desperate move to get closer to the playful man. A stuttering whine left Dean’s lips as Cas leaned forward and began to suck in the spot behind Dean’s left ear. 

Dean arched into the nips at his neck, dragging Jimmy closer so he could run his hand up the other man’s back, feverishly kissing him as Jimmy’s hand came down to press against Dean’s length, dragging a heaving groan from the man as he bucked into the hand, confined within too tight jeans. 

The mouth at his neck shifted and nipped his ear. “Pay attention to the road.” Castiel commanded and reached over to tug Jimmy away from Dean’s mouth so that Dean could drive now that the light had changed to green. Jimmy whined and turned to drag Castiel forward over the bench seat and kissed him feverishly, dragging a whimper out of Dean who kept glancing over at them to watch. 

“Jesus…” Dean managed as Jimmy whimpered and backed away to yank Castiel over the bench and across his body, all three men crowded into the front of the car with one twin now straddling the other as he kissed him demandingly. Cas pulled up and cupped Jimmy’s cheek, “What do you want, Jimmy?” His voice was commanding and rough and his twin sprawled out wantonly underneath him. 

Jimmy shifted and rocked his hips up into Castiel’s, head thrown back over the back of the bench seat as he dragged his own shirt up, showing off several possessive bite marks. He whimpered when Castiel reached down to press his fingers into one with a smirk, “own me,” Jimmy demanded as he arched up again and Dean reached over as if to touch them before pulling his hand back regretfully to turn them toward the address the men had given him. Eyes swiveling back and forth from the twins to the road and his own whimper echoing out in the car’s interior. 

Castiel’s lips quirked and he ducked down to suck another harsh mark into the smooth tanned skin next to Jimmy’s nipple, whimpers and cries erupting as Jimmy arched into the mouth, “Cas! God yes, Castiel!!” falling like prayers from his mouth. 

Castiel pulled back finally, skin stretching, trapped between his teeth to show the purpling mark left over his heart. “I already do own you… don’t I?” he asked fondly and chuckled darkly. 

“Yeeees.” Jimmy cried as he reached down to press his own finger into the new mark with a keen. He arched up as Castiel kissed him and then shook his head down at the twin while Dean parked the car, the engine quickly shutting off and leaving them panting in the suddenly silent car. “What else do you want?” He asked Jimmy, blue eyes locked to blue before Jimmy broke the gaze to glance over at Dean’s wrecked expression and grinned, “I want you to fuck him while he fucks me,” He decided playfully and when that drew a whimper from the green eyed man watching them, added, “I want to watch you spank him while I suck his cock.” 

“Son of a… Yes god yes.” Dean declared it in a raspy, desperate tone and Castiel looked over to consider him before reaching out to quickly grab Dean and pull him over next to them and kissed him filthily.

Dean pushed himself closer, surging up against them as Jimmy slithered a hand around his back and into the waist of his jeans to tease fingers against his ass earning a whimper from Dean, “please,” he begged, voice wrecked.

Castiel pulled back, eyes lit darkly with promises. “Please what?” he coaxed.

Dean groaned brokenly as his face flushed, “Please Cas, please?” 

Castiel chuckled and reached up to grip Dean’s chin, lifting his face up to face his own, grip strong and just shy of bruising, “Please… what?” He repeated, voice lower and eyebrow lifting as Jimmy whimpered under him and shifted up to kiss Castiel’s throat. 

Dean’s eyes widened in shock, cheeks staining even darker with his blush and he stuttered, a whimper falling when Castiel’s eyebrow rose, transfixed. “Please, Sir.” 

Castiel’s lips spread slowly. “Good boy, Dean… I think we can arrange that.” He agreed huskily as he leaned in for another kiss. 

~~~

Castiel had climbed out of the car and dragged Jimmy out before Dean slid after them, pocketing the keys as he closed the heavy door and took a shuddering breath in the cool night air. Jimmy pressed forward and kissed Dean gently on the lips as he linked fingers with the taller man and then tugged him up the walk and into the house. Dean wanted a chance to look around, size it up but was immediately captured in another kiss as Jimmy shoved him back against the wall and pressed forward, mouth angling to nip at his neck and rock their hips together. Castiel came in the house behind them, shutting the door and humming as he watched the men rock against each other, hands feverishly tugging at shirts and belt loops. “You make a very pretty picture with our new friend, Janiel.” he intoned and Jimmy ripped his mouth away to scowl at Castiel. “You know I hate that,” he whined in response while Dean rested his head back against the wall and gasped. 

Castiel’s lips curled in a satisfied smirk. “I know, beloved. But it is very fun to make you pout,” he explained as he toed off his shoes and then walked past them slowly, turning as he entered the doorway to the living room and holding out both of his hands in silent invitation. Jimmy immediately took Castiel’s hand and then glanced back at Dean. 

Dean stared at them through hooded green eyes, his lip caught between his teeth and body tense for a moment. He was losing some of his liquid courage and with a bit of a break since the intensity of the car, he was hesitating, eyes searching theirs for several long moments before finally reaching out to take Castiel’s hand and let himself be dragged into the soft light of the living room, the LED candles on the table casting the room in a warm glow. “Knees, Jimmy.” Castiel murmured as he dragged Dean close for a couple of gentle kisses, “my brother,” he managed between two gentle presses of lips, “is very dear to me, I try to give him all that he desires. You’ll help me with that, won’t you Dean?” 

Dean shivered at the raspy tone of the words and nodded wordlessly, then gasped as he was turned around in Castiel’s arms, hands reaching down to his hips and dragging up under his shirt to lift it up and over his head. He lifted his arms to help and relaxed back as another shirt fell behind him and he was suddenly dragged back against a warm chest, Castiel’s right arm coming up and across his chest to settle, gripping Dean’s left arm. 

Jimmy shifted forward on his knees, leaning his head against Dean’s hip and sighing in pleasure before mouthing over his straining erection through the rough denim that separated them. 

“Slowly, Pet,” Castiel bade and Jimmy peeked up through dark lashes at the two men staring down at him and flashed them a wide smile while reaching up to slip the button free then surging forward to grip the zipper pull with his teeth and slowly ease it down, breath fanning over Dean. 

Dean moaned and sagged against Castiel and the tight grip that held him up as his cock sprang free once the zipper was opened all the way, earning him a small delighted laugh from Jimmy as he traced his tongue up the underside of Dean’s hard length. “Fuck me,” Dean breathed and earned a chuckle right at his left ear before soft lips teased against the shell of it. 

“In due time,” Castiel promised as he watched Jimmy tug Dean’s jeans down over thick thighs before pressing forward to pop his lips over Dean’s cock and suck firmly. Dean’s body arched up at the sudden intense suction and his back arched, a wordless shout tearing from him as he scrambled his arms up to hold onto Castiel’s arm like an anchor. 

Jimmy began to move, tongue playing against the pulsing vein in Dean’s cock and teasing against the head as he pulled back. Dean sobbed and closed his eyes, letting his head rest back against Castiel’s strong shoulder. It was different, he couldn’t stand up straight which had him splayed open and vulnerable for Jimmy who’s hands came up to scratch Dean's thighs, earning another hoarse cry. 

And then, Castiel began to talk. 

“Look at you, so pretty Dean. You look so good with your cock disappearing down my brother’s throat like that,” Cas praised as his hand came down to stroke Dean’s ass, grabbing his left cheek and squeezing firmly before smacking him, earning a moan from Jimmy in response as Dean’s cock thrust down his throat. 

“All panting and pleading and crying out. Do you like how he feels with his lips wrapped around you? Does it make you want to spill down his throat?” Another sharp slap that sent Dean’s hips bucking forward with a whimper. “You’re not allowed to do that,” Castiel said firmly; another three sharp strikes landing, each jerking Dean’s hips forward into Jimmy’s hot mouth as he sucked firmly and Dean sobbed. 

“You’re not allowed to cum until I’m buried balls deep inside you,” he added as Dean’s cries grew louder. Suddenly, the hand spanking Dean stopped so he could reach around to bury in Jimmy’s hair and drag him off of Dean’s dick quickly. “If you make him cum, I’ll punish him and then punish you twice, Janiel,” came the warning growl. 

Jimmy panted and turned to press a strained kiss to Cas’ inner wrist before shifting forward to rest his head against Dean’s thigh, his own hand coming down to squeeze himself for relief. 

“Bedroom.” Castiel rasped and Jimmy stood eagerly, arching against Dean for a kiss before sauntering off to obey that command. Castiel finally released Dean from the iron grasp on his arm and spun him to kiss him demandingly, deepening the kiss when Dean staggered into him drunkenly. “Cas,” Dean whimpered and arms came up around slender shoulders in response. 

Castiel snaked an arm around Dean’s waist and led him back to the bedroom, his eyes darkening in pleasure at the sight of his twin. Jimmy had elected not to wait for them, and instead had thrown his clothes to the floor and crawled up on the bed with lubricant. Now he was kneeling, facing away from the doorway with two fingers working himself open as he moaned into the pillow.

Castiel pressed Dean forward wordlessly, eyes lit with desire as Dean hiked himself up on the bed and ran his hands up over Jimmy’s thighs to cup his cheeks and spread them so he could watch. “You’re fuckin’ beautiful,” Dean murmured softly, transfixed on the sight of fingers pumping in and out. 

Jimmy panted and screwed his eyes shut, arching his back up to offer himself in response, fingers pressing in again as deep as he could manage with the angle,“I’m gonna be prettier when you’re shoving that cock in me.”

Dean hissed in response and picked up the lubricant to wet a finger before pushing it in beside Jimmy’s earning a shout from the dark-haired man as Castiel slowly stalked forward, the sound of a button popping and a zipper unfastening arresting both men as they turned as one to face the Dominant stalking forward.

Dean shivered, his body freezing as he watched Castiel approach the bed. The older man stalked forward soundlessly and he reached out to tease a hand up Dean’s calf from his ankle before gripping it and yanking hard, smirking as Dean yelped and collapsed on the bed, finger pulling from Jimmy’s entrance quickly, earning a sharp cry in response. 

Dean panted and flipped on his back to look up at Castiel who rewarded him with a small smile before dragging Dean close with his ankles, planting them at the edge of the mattress then gripping his hips to pull him flush against Cas’ denim clad hips. 

Castiel smirked down at Dean and bent forward, forcing the other man's thighs wide as he grabbed the lubricant and stood straight again, opening the bottle with a wet snap and pouring a small stream of the slick down Dean's cock, stroking him firmly twice to coat him then pulling his hand away as Dean cursed and slammed his head back into the bedding with a grunt of disappointment.

Castiel spanked Dean’s thigh sharply in response, though his eyes were glittering in amusement as Dean arched up into the strike rather than shy away from it. "Warm his cock for him Jimmy, don't arouse him… Just keep him ready while I open up his pretty hole for me." Castiel's words spilled out in a gravely rumble, drawing whimpers from both men as Jimmy quickly moved to straddle Dean, steadying himself on the man's chest and pinching his nipples playfully while Castiel gripped Dean's cock and guided it into Jimmy. 

Jimmy threw his head back with a low wordless cry of pleasure at the stretch that came with minimal prep and he sank down until he was fully seated. He paused there, chest heaving, light dancing over the faint sheen of glitter and sweat as he leaned down to kiss Dean in between panted whimpers. 

Dean hardly had a chance to catch his breath or adjust to the hot wet heat that squeezed around him so tightly before a slick finger grazed his entrance and teased there for a moment before pressing in and sinking deep. 

Dean threw his head back, eyes screwing shut as he fisted hands into the blankets, whining as Jimmy leaned over to bite sharply at his shoulder then lay nips and kisses along the column of his neck. 

Jimmy began to suck a bruising mark behind Dean's ear, in the same place Castiel had marked earlier in the car, "I can feel you pulsing inside of me, Dean. You're so perfect, baby… does he feel good? I bet you can't wait for him to push his cock inside you. Can't wait to be full, can you Dean? We're going to ruin you, make it impossible to forget us. We're going to sear the memory of us in your soul."

Dean's response ripped out with the addition of another finger and Jimmy laughed when Dean bucked backwards in desperation. "God, Cas… Look at him," Jimmy breathed as Castiel stretched Dean and leaned forward to press kisses across Jimmy's shoulder. "He's so pretty like this, all begging and fucked out, I want to keep him." Jimmy groaned and rocked down on Dean's cock as the green-eyed man thrashed his head and broke. 

"Please… please Cas, Jimmy please." Teary green eyes lifted to lock into theirs. "Please Sirs, please fuck me, I'm ready, so ready," his voice was wrecked as he reached up to stroke hands up Jimmy's thighs and squeezed around Castiel's fingers. 

"God, Cas…" Jimmy rasped as Castiel quickly added a third finger and nodded. "Yes Dean," he soothed him gently before pulling his hand free only to earn a sob from Dean in response as he slicked himself and pressed forward. "Move." Cas murmured in Jimmy's ear and waited as Jimmy moved forward to brace himself on Dean's shoulders as he lifted himself up and then rocked back down on Dean's cock. 

Castiel spread Dean's cheeks and positioned himself against Dean and when Jimmy rocked up and back down, sank into Dean in tandem with his twin, a deep groan dragging out of Castiel’s throat as he pressed closer and began to meet Jimmy’s rhythm, hands coming down to grip and anchor Dean’s hips so that he could rock into him smoothly, bottoming out on the third thrust as Dean gritted his teeth and sobbed, throwing one of his arms over his face to hide the sudden tears springing in his eyes. “God dammit… yes. God don’t stop, please don’t stop.” Dean managed to beg them through clenched teeth as he rocked, struggling to figure out if he wanted to fill or be filled more. 

Jimmy sighed in pleasure as the thrusting sent pleasure into his gut with each thrust, leaning forward to get a deeper thrust and grunting when it caused Dean’s cock to brush just right over his prostate. “Cas… Angel… god not gonna last.” Jimmy managed and Dean dragged his hand down from his face, streaking tears across freckled cheeks to grip Jimmy’s cock. “Please…” He managed though he didn’t appear to know what he was asking for even as he begged for it. 

Castiel sped his thrusts in response, pleasure curling low in his gut as he watched Jimmy rock back desperately, Dean disappearing into him. Castiel lifted one hand from Dean’s hip to spread Jimmy’s cheek lightly, groaning as he watched Dean rock into his brother with each thrust and ran his thumb across the rim of Jimmy’s entrance, dragging broken cries from both men as he snapped his hips forward and pressed his thumb in beside Dean. 

“FUCK, Cas! Dean!” Jimmy wailed as he rocked back once more and came hard, clenching around Dean and Cas, seed spilling over Dean’s stomach as he bent to kiss Dean sloppily. It was enough to send Castiel’s hips rocking faster, harder inside of Dean, yanking the younger man's legs up over his forearms so he could give into the chase of pleasure and release. Apparently it was enough for Dean because he cried out against Jimmy’s lips, hand coming up to grip the back of his neck to hold him close as he buried his face in Jimmy’s neck and came, still buried in Jimmy who gave a filthy moan and rocked back appreciatively in response to the pulsing release filling him. 

Dean tightened so hard around Cas when he came that blue eyes snapped shut, feeling that edge of almost pain as he dug his fingers into Dean’s thighs and allowed himself to cum with three last, weak thrusts, burying himself deep as he bent to rest his head on Jimmy’s back, kissing the ridge of a vertebrae tenderly. He paused there, arms sliding up Dean’s legs to curl around both of them before carefully pulling free of Dean, smiling at the grumbled protest he received for his efforts. He left them there as he went to get two washcloths, wetting them and snagging a towel before stumbling back. 

Jimmy had pulled up off of Dean but was still curled in Dean’s arms, kissing him lightly. Castiel watched them before stepping forward, cleaning his brother of cum and lube before nudging him off of Dean to wipe his stomach clean then tossing that cloth and focusing on Dean with the other, drying them both gently as he leaned down to kiss Dean lightly then Jimmy a little more deeply. “Stay with us tonight?” He asked as Jimmy crawled up to sprawl over the pillows and reach for Dean. 

Dean smiled up at Cas and nodded once, shifting to let Jimmy pull him into his arms before Castiel turned out the lights and moved up to curl up behind him, dragging the blankets up over them with a sigh. There was a soft comfortable silence then Jimmy’s voice sounded in the dark. “Damn.”

Dean chuckled and shifted to push back into Castiel’s hips and drag Jimmy closer so he could be more firmly pressed between them. “Hell yeah.” He muttered sleepily. 

Castiel just smiled and closed his eyes in contentment. They could talk about forever tomorrow. After all, Cas always made sure that Jimmy got what he wanted.


End file.
